Learning from failures

Welcome back to our weekly series, The Winning Entrepreneur: Your Weekly Guide to Success, a program designed for ambitious entrepreneurs and people who want to turn their ideas into successful businesses. Last week, we talked about how you don’t have to be number one to make an impact. Today, we’re looking at how to learn from failure.

Making mistakes is part of growth and often in our country it is associated with a completely negative concept. The best entrepreneurs, creatives and leaders do not fear failure: they know how to use it as a springboard and “fuel for growth”. There is a chasm between those who face a setback and are crushed by the experience and those who, instead, use the negative experience to build something greater. If you have ever felt the weight of a failure, remember that the difference between those who give up and those who triumph is not the absence of mistakes, but the ability to use them to your advantage.

Using Failures as Growth Accelerators

In Silicon Valley, failure is almost a hallmark of experience. Reid Hoffman, co-founder of LinkedIn , once said that “ if you’re not embarrassed by the first version of your product, you launched too late.” The point is not to create imperfections on purpose, but to recognize that every obstacle overcome is a step toward a better version of yourself or your project.

Sarah Blakely, founder of Spanx , describes how her father would ask her every day, “ What didn’t work for you today ?” Growing up with this mindset, she learned to see challenges as an essential part of learning. When her first Spanx prototypes were rejected, instead of giving up, she took note of each rejection and refined the product. Today, she is one of the most successful entrepreneurs in the world.

Even in the world of sports, Michael Jordan admits to losing over 300 games and missing over 9,000 shots. Yet, those very mistakes made him the greatest basketball player ever. If you feel stuck in the fear of making a mistake, remember that every failed attempt brings you closer to being the best version of yourself.

Techniques for structured experimentation and fast learning

Not all failures are created equal. Some consume resources and undermine projects, while others teach valuable lessons without harming the enterprise. The key is to experiment in a controlled manner and with a learning system.

Jeff Bezos popularized the concept of “reversible mistakes.” If a decision can be undone without irreparable damage, it should be made quickly and field-tested. If it is irreversible, it requires more analysis and testing. Amazon has experimented with dozens of unsuccessful products, from the Fire Phone to dozens of unsuccessful marketplaces, but each attempt has allowed it to refine future strategies. Amazon has also changed its brand five times, and most analysts did not believe Bezos’s project could survive.

Elon Musk also applies a similar method: rapid and iterative experimentation. With SpaceX , he accepted the loss of the first rockets sent into space in order to collect data to improve subsequent versions. Without these initial attempts, we would not have the reusable Falcon 9s that have revolutionized the space industry today.

If you want to apply this principle to your life, try the “mini-bet” technique: instead of launching an entire project, test a smaller version of it. Want to open a restaurant? Experiment with a series of private dinners or a food truck first. Want to write a book? Start with a series of articles. Reduce risk, learn quickly, and improve with each iteration.

Building Inner Strength Through Continuous Challenges

Setbacks can ruin a reputation or make it stronger. The difference is how you handle them. Steve Jobs was forced out of Apple , the company he created. Instead of letting that get him down, he founded Pixar and NeXT , then returned to Apple to lead it to global success. This journey not only demonstrated his ability to innovate, but reinforced his image as a resilient visionary.

Even Oprah Winfrey was kicked off television for not being “fit for news.” If she had stopped at that rejection, she would not have become the most influential woman in media. She turned her vulnerability into a strength, creating a format based on empathy and emotional connection.

To build a solid reputation even through difficult times, transparency is key. If you admit mistakes, explain what you've learned, and show how you're improving, others will see your journey as a story of growth, not defeat.

When Action is Better than Analysis Paralysis

Fear of failure can lead to analysis paralysis, a condition in which excessive planning and evaluation prevents any concrete action. This state of mind harms more people than the failures themselves. The truth is that the real risk is getting trapped in an endless cycle of analysis. James Dyson created 5,126 prototypes of his vacuum cleaner before he found the right one. If he had stopped to overanalyze each failure, there would be no multi-billion dollar company with his name today.

Even in the financial world, Ray Dalio, founder of Bridgewater Associates , one of the world's largest hedge funds, built an empire thanks to his initial mistakes. After suffering significant losses due to incorrect assessments, he developed a system to make decisions based on data and not on ego. Today, he is one of the most respected investors in the world.

A particularly illuminating case is that of Giorgio Armani, who began his career as a window dresser and buyer for La Rinascente. After working as a freelance designer for various fashion houses, he decided to launch his own line in 1975, at the age of 41. His first attempts to create a collection were met with skepticism by the Milanese fashion establishment, who considered his style too minimalist and “not very Italian.” Instead of conforming to expectations, Armani learned from these criticisms and strengthened his vision of more essential and wearable fashion. What initially seemed like a misjudgment of the market turned out to be his greatest strength, leading him to revolutionize the world of fashion and build a luxury empire.

For a deeper dive into these concepts, Carol S. Dweck’s Mindset: The New Psychology of Success explores how our mindset influences our ability to learn from mistakes. Chess grandmaster Josh Waitzkin’s The Art of Learning reveals how to turn every challenge into an opportunity for improvement. Daniel Kahneman’s Thinking, Fast and Slow helps us understand how our decision-making processes influence our ability to deal with obstacles. And for a more practical approach, David Epstein’s Range: Why Generalists Triumph in a Specialized World demonstrates how experience in multiple fields and mistakes in multiple directions can lead to extraordinary innovation.

If you want to stand out, you must be willing to learn from your mistakes better than others. You must also have the stomach to tolerate constant adversity and stress. Don't avoid obstacles, but face them in a way that teaches you something valuable. Those who can embrace adversity and benefit from it not only grow faster, they become unstoppable.